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Related Concept Videos

Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.1K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
4.1K
Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

2.4K
Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in 1,5-hexadiene, referred...
2.4K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.5K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.5K
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

2.1K
Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Intermolecular transposed Paternò-Büchi reactions enabled by triplet sensitization.

Tahoe A Fiala1, Omar A Solis1, Jesse B Kidd1

  • 1Department of Chemistry, University of Wisconsin-Madison 1101 University Avenue Madison WI 53706 USA tyoon@chem.wisc.edu.

Chemical Science
|November 27, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a new photocatalytic method for transposed Paternò-Büchi cycloadditions using visible light. This approach utilizes a photosensitizer for selective triplet energy transfer, enabling broader synthetic applications.

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Area of Science:

  • Organic Photochemistry
  • Cycloaddition Reactions
  • Photocatalysis

Background:

  • The Paternò-Büchi reaction is a classic organic photoreaction forming oxetanes from excited carbonyls and ground-state alkenes.
  • The transposed Paternò-Büchi reaction, involving excited alkenes and ground-state carbonyls, is less understood and underdeveloped.

Purpose of the Study:

  • To develop a visible light photocatalytic method for transposed Paternò-Büchi cycloadditions.
  • To enable a more general and thorough investigation of the synthetic utility of this reaction.

Main Methods:

  • Employing a photosensitizer for selective triplet energy transfer to the alkene.
  • Utilizing visible light as the energy source for the photocatalytic process.
  • Investigating the scope and limitations of the developed reaction conditions.

Main Results:

  • Successful implementation of a visible light induced photocatalytic approach for transposed Paternò-Büchi reactions.
  • Demonstrated selective triplet energy transfer to the alkene component by the photosensitizer.
  • Established general reaction conditions facilitating comprehensive exploration of synthetic opportunities.

Conclusions:

  • The developed photocatalytic strategy provides a valuable new tool for accessing oxetanes via transposed Paternò-Büchi cycloadditions.
  • This method broadens the synthetic applicability of the transposed Paternò-Büchi reaction under mild, visible light conditions.